DE3101703A1 - Verfahren zur herstellung von buten-1 aus einer c(pfeil abwaerts)4(pfeil abwaerts) -kohlenwasserstoff-fraktion - Google Patents
Verfahren zur herstellung von buten-1 aus einer c(pfeil abwaerts)4(pfeil abwaerts) -kohlenwasserstoff-fraktionInfo
- Publication number
- DE3101703A1 DE3101703A1 DE19813101703 DE3101703A DE3101703A1 DE 3101703 A1 DE3101703 A1 DE 3101703A1 DE 19813101703 DE19813101703 DE 19813101703 DE 3101703 A DE3101703 A DE 3101703A DE 3101703 A1 DE3101703 A1 DE 3101703A1
- Authority
- DE
- Germany
- Prior art keywords
- butene
- fraction
- hydrocarbons
- isobutene
- butane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 229930195733 hydrocarbon Natural products 0.000 title claims description 32
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 29
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 72
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 19
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 18
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 238000005984 hydrogenation reaction Methods 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000000605 extraction Methods 0.000 claims description 12
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 12
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000001282 iso-butane Substances 0.000 claims description 9
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 238000000895 extractive distillation Methods 0.000 claims description 5
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- -1 acetylene hydrocarbon Chemical class 0.000 claims description 2
- 239000001273 butane Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 238000006317 isomerization reaction Methods 0.000 claims description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229940116441 divinylbenzene Drugs 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000005673 monoalkenes Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical class C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical class O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 229910052596 spinel Inorganic materials 0.000 description 1
- 239000011029 spinel Substances 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/163—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/005—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
- C07C7/05—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds
- C07C7/08—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by extractive distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/14875—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds
- C07C7/14891—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/163—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation
- C07C7/167—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation for removal of compounds containing a triple carbon-to-carbon bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR8001573A FR2474024A1 (fr) | 1980-01-23 | 1980-01-23 | Procede de production de butene-1 a partir d'une coupe c4 d'hydrocarbures |
Publications (1)
Publication Number | Publication Date |
---|---|
DE3101703A1 true DE3101703A1 (de) | 1981-11-26 |
Family
ID=9237850
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19813101703 Withdrawn DE3101703A1 (de) | 1980-01-23 | 1981-01-21 | Verfahren zur herstellung von buten-1 aus einer c(pfeil abwaerts)4(pfeil abwaerts) -kohlenwasserstoff-fraktion |
Country Status (7)
Country | Link |
---|---|
JP (1) | JPS56104824A (no) |
BE (1) | BE887125A (no) |
DE (1) | DE3101703A1 (no) |
FR (1) | FR2474024A1 (no) |
GB (1) | GB2068408B (no) |
IT (1) | IT1136559B (no) |
NL (1) | NL8100288A (no) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3426349A1 (de) * | 1983-07-28 | 1985-02-14 | Snamprogetti S.P.A., Mailand/Milano | Verfahren zur gewinnung von 1-buten fuer polymerisationszwecke |
DE3620481A1 (de) * | 1985-06-19 | 1987-01-02 | Air Prod & Chem | Verfahren zur herstellung von hochreinem buten-1 aus einem n-butan enthaltenden ausgangsmaterial |
WO2019007781A1 (de) * | 2017-07-04 | 2019-01-10 | Thyssenkrupp Industrial Solutions Ag | Verfahren und anlage zur trennung von c4-kohlenwasserstoffen durch extraktive destillation |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2517668A1 (fr) * | 1981-12-08 | 1983-06-10 | Inst Francais Du Petrole | Procede d'obtention conjointe de butene-1 de haute purete, de supercarburant et de combustible pour carbureacteur |
FR2508437A1 (fr) * | 1981-06-26 | 1982-12-31 | Inst Francais Du Petrole | Procede d'obtention conjointe de butene-1 de haute purete et de supercarburant a partir d'une coupe c4 olefinique |
FR2508899A1 (fr) * | 1981-07-02 | 1983-01-07 | Inst Francais Du Petrole | Procede d'obtention de butene-1 de haute purete a partir d'une coupe c4 olefinique |
DE3265069D1 (en) * | 1981-06-26 | 1985-09-05 | Inst Francais Du Petrole | Process for simultaneously obtaining high-purity butene-1 and a premium grade fuel from an olefinic c4 cut |
US4515661A (en) * | 1981-10-13 | 1985-05-07 | Nippon Zeon Co. Ltd. | Process for separating highly pure butene-1 and butene-2 |
FR2515171B1 (fr) * | 1981-10-28 | 1986-12-26 | Inst Francais Du Petrole | Procede de valorisation des coupes c4 olefiniques |
JPS5892625A (ja) * | 1981-11-27 | 1983-06-02 | Nippon Zeon Co Ltd | C↓4炭化水素留分より高純度ブテン−1又はブテン−1/イソブテン混合物の分離方法 |
FR2520356B1 (fr) * | 1982-01-26 | 1987-09-18 | Inst Francais Du Petrole | Procede de valorisation des coupes c4 olefiniques |
JPS59193870U (ja) * | 1983-06-08 | 1984-12-22 | 東北金属工業株式会社 | 単結晶製造るつぼ |
JP2842091B2 (ja) * | 1992-09-11 | 1998-12-24 | 日本ゼオン株式会社 | 高純度1−ブテン及び2−ブテンの取得方法 |
FR2710907B1 (fr) * | 1993-10-08 | 1996-01-05 | Inst Francais Du Petrole | Procédé de production d'éthers tertiaires à partir d'une charge de craquage catalytique comprenant deux étapes de distillation extractive. |
DE10233385A1 (de) | 2002-07-23 | 2004-02-12 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Propylenglykolen |
DE102005062700A1 (de) * | 2005-12-28 | 2007-07-05 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von 1-Buten aus technischen Mischungen von C4-Kohlenwasserstoffen |
CN110590492B (zh) * | 2019-10-10 | 2021-03-26 | 大连理工大学 | 一种综合利用醚后碳四的甲基叔丁基醚生产工艺 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB866395A (en) * | 1959-01-09 | 1961-04-26 | Bayer Ag | A process for the selective hydrogenation of unsaturated compounds present in c -fractions |
DE1926503C3 (de) * | 1968-05-27 | 1975-03-20 | Maruzen Oil Co. Ltd., Osaka (Japan) | Verfahren zu selektiven Hydrierung von mehrfach ungesättigten Kohlenwasserstoffen |
US3681202A (en) * | 1970-06-01 | 1972-08-01 | Petro Tex Chem Corp | Method of purifying unsaturated hydrocarbons by extractive distillation with side stream removal and solvent mix |
DE2802198A1 (de) * | 1978-01-19 | 1979-07-26 | Basf Ag | Verfahren zur gewinnung von isobuten aus isobuten enthaltenden c tief 4 -kohlenwasserstoffgemischen |
-
1980
- 1980-01-23 FR FR8001573A patent/FR2474024A1/fr active Granted
-
1981
- 1981-01-19 BE BE1/10103A patent/BE887125A/fr not_active IP Right Cessation
- 1981-01-19 IT IT19190/81A patent/IT1136559B/it active
- 1981-01-21 DE DE19813101703 patent/DE3101703A1/de not_active Withdrawn
- 1981-01-21 NL NL8100288A patent/NL8100288A/nl not_active Application Discontinuation
- 1981-01-22 GB GB8101983A patent/GB2068408B/en not_active Expired
- 1981-01-23 JP JP954081A patent/JPS56104824A/ja active Pending
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3426349A1 (de) * | 1983-07-28 | 1985-02-14 | Snamprogetti S.P.A., Mailand/Milano | Verfahren zur gewinnung von 1-buten fuer polymerisationszwecke |
DE3620481A1 (de) * | 1985-06-19 | 1987-01-02 | Air Prod & Chem | Verfahren zur herstellung von hochreinem buten-1 aus einem n-butan enthaltenden ausgangsmaterial |
DE3645144C2 (no) * | 1985-06-19 | 1991-04-18 | Air Products And Chemicals, Inc., Trexlertown, Pa., Us | |
WO2019007781A1 (de) * | 2017-07-04 | 2019-01-10 | Thyssenkrupp Industrial Solutions Ag | Verfahren und anlage zur trennung von c4-kohlenwasserstoffen durch extraktive destillation |
Also Published As
Publication number | Publication date |
---|---|
GB2068408A (en) | 1981-08-12 |
IT8119190A0 (it) | 1981-01-19 |
FR2474024B1 (no) | 1984-09-21 |
IT1136559B (it) | 1986-09-03 |
BE887125A (fr) | 1981-07-20 |
JPS56104824A (en) | 1981-08-20 |
GB2068408B (en) | 1983-06-08 |
FR2474024A1 (fr) | 1981-07-24 |
NL8100288A (nl) | 1981-08-17 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
8141 | Disposal/no request for examination |